4-Chloropyridine → HCID 67379602, compound

HRID 1643445Notes

Reaction equation

C([CH:5]1[C:9]2([CH2:13][CH2:12][NH:11][CH2:10]2)[CH2:8][CH2:7][N:6]1[C:14]([OH:16])=[O:15])(C)(C)C.C(N([CH:23]([CH3:25])[CH3:24])C(C)C)C.Cl[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1.[C:33](=O)(O)[O-].[Na+]>CC(O)C>[N:30]1[CH:31]=[CH:32][C:27]([N:11]2[CH2:12][CH2:13][C:9]3([CH2:5][N:6]([C:14]([O:16][C:23]([CH3:25])([CH3:33])[CH3:24])=[O:15])[CH2:7][CH2:8]3)[CH2:10]2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl 2,7-diaza-spiro[4.4]nonane-2-carboxylic acid (4.419 mmol, 1 eq) and N-ethyl-diisopropylamine (17.674 mmol, 4 eq) were dissolved in 2-propanol (8 ml), 4-chloropyridine (13.256 mmol, 3 eq) was added and the mixture was heated at 90° C. for 16 h. Saturated sodium bicarbonate solution (20 ml) was added and the phases were separated. The aqueous phase was extracted with ethyl acetate (4×20 ml) and the combined org. phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. After purification by column chromatography (silica gel, ethyl acetate/methylene chloride/methanol/ammonia (25 aq) (100:100:25:1), the desired product was obtained as a pale brown oil. Yield: 0.67 g (50%)

Workup

customthe phases were separated
extractionThe aqueous phase was extracted with ethyl acetate (4×20 ml)
washphases were washed with saturated sodium chloride solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customAfter purification by column chromatography (silica gel, ethyl acetate/methylene chloride/methanol/ammonia (25 aq) (100:100:25:1)

Sources & evidence

ORD record: ord-f05a87d009384923902d64c668a7d645
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119805B2

Reaction notes

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